Potassium Carbonate → (2-Chlorophenyl)(2,2-diethoxyethyl)sulfane

HRID 2042344Notes

Reaction equation

HRID 2042344 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].Br[CH2:10][CH:11]([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH2:10][CH:11]([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 80599o-Chlorothiophenol

Product 1

HCID 59133109(2-Chlorophenyl)(2,2-diethoxyethyl)sulfaneYield 80%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-chlorobenzenethiol (5.0 g, 34.5 mmol) in acetone (35 mL) was added 2-bromo-1,1-diethoxyethane (7.15 g, 36.3 mmol) followed by potassium carbonate (9.55 g, 69.1 mmol). The mixture was heated at reflux for 3 h. then cooled to rt, filtered and the filtrate evaporated under reduced pressure to yield the crude product. This material was purified by chromatography over silica gel eluting with ethyl acetate in hexanes (0→2%) to afford pure 1-chloro-2-(2,2-diethoxyethylsulfanyl)benzene (7.3, 80%). 1H NMR (400 MHz, CDCl3) δ=1.20 (t, J=7.07 Hz, 6H), 3.15 (d, J=5.56 Hz, 2H), 3.51-3.61 (m, 2H), 3.63-3.74 (m, 2H), 4.69 (t, J=5.56 Hz, 1H), 7.12 (td, J=7.58, 1.52 Hz, 1H), 7.20 (td, J=7.58, 1.52 Hz, 1H), 7.36 (dd, J=7.83, 1.52 Hz, 1H), 7.39 (dd, J=8.08, 1.52 Hz, 1H); MS (ES+): m/z 187.17 [M-74].

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 h.
  3. filtrationfiltered
  4. customthe filtrate evaporated under reduced pressure
  5. customto yield the crude product
  6. customThis material was purified by chromatography over silica gel eluting with ethyl acetate in hexanes (0→2%)

Sources & evidence

ORD record
ord-048a3e5b36bf46f3935c5a21163c6d52
Source dataset
uspto-grants-2013_11
Patent number
US08586546B2

Reaction notes

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